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1H NMR studies of intramolecular hydrogen bonding in N-(pyridyl)amides of 6-methylpicolinic acid N-oxide

✍ Scribed by Bogumil Brzezinski

Publisher
John Wiley and Sons
Year
1979
Tongue
English
Weight
231 KB
Volume
12
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The ^1^H NMR spectra of seven N‐(pyridyl)amides of 6‐methylpicolinic acid N‐oxide in chloroform were obtained. The influence on the chemical shifts of the NH protons of temperature, concentration and the CH~3~ substituent in the pyridine ring was studied. The NH protons were found to be shifted to low fields (∼14 ppm) owing to the formation of strong intramolecular hydrogen bonding. The influence of the pyridine ring on the chemical shift of the NH proton is comparable with the inductive effect of the p‐nitrophenyl group. The hindered rotation around the N‐pyridyl bond of N‐(α‐pyridyl)amides of 6‐methylpicolinic acid in solution is discussed.

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